


Fifty Shades of Destiel Cringe

by SerLadyJenn



Series: Valentine's Day Horror Shit [6]
Category: Supernatural
Genre: BDSM, Cas as the hot boss dom, Cas is a take no shit top, Dean as the assistant chick, Dean is a bottom fight me, Dean is secretly a slut, How Do I Tag, Inspired by Fifty Shades of Grey, Lily I love you but it was 2am, M/M, Someone stop me, fifty shades of cringe, haha i already was, hahahaha i am unstoppable, it'll fuck you up, more like fifty shades of cringe, not really but i tried, tag gore, this was rushed you can tell, ya'll don't write in the middle of the night, you know what that's what I'm gonna name it
Language: English
Status: Completed
Published: 2020-02-24
Updated: 2020-02-24
Packaged: 2021-02-27 20:26:49
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 1,443
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/22871704
Author URL: https://archiveofourown.org/users/SerLadyJenn/pseuds/SerLadyJenn
Summary: Dean uses his perky tits to land a new job as Castiel's hot slutty assistant. Mr. Novak can't help but be fascinated by such bountiful rounds of moobs in his face and demands Dean to be his new hungry slut. Dean immediately drops to his knees with many cringey sexily uwu noises to suck his boss' nice juicy cock.No. I'm sorry, I can't. Here's the real summary:Dean starts his new job as Mr. Novak's assissant. He oh so desperately wants to make a good impression so when Mr. Novak calls him in for an important assignment, Dean of course isn't gonna say no.
Relationships: Castiel/Dean Winchester
Series: Valentine's Day Horror Shit [6]
Series URL: https://archiveofourown.org/series/1642642
Comments: 8
Kudos: 22





	Fifty Shades of Destiel Cringe

**Author's Note:**

  * For [lilyanna](https://archiveofourown.org/users/lilyanna/gifts).



> For Lily, my first child (Not really but you get it)
> 
> By continuing to read you agree that any mental or physical harm caused by this writing is in no way responsible by the author.

Newly hired Dean Winchester was excited to start working with his new employer, Castiel Novak. He had prepared furiously since first being hired a few days ago, taking pointers from Mr. Novak’s last assistant who left due to getting married. Dean learned how Mr. Novak took his coffee (just black), what he preferred for lunch (almost anything from a local vegan place which reminded him of Sam), and how he liked his dry cleaning done. Dean Winchester was all set to be the model personal assistant and nothing was going to get in his way, not even being distracted by the beauty that is Castiel Novak. 

Dean was just about to sit at his desk when the intercom chimed which meant it was Mr. Novak. “Dean, come into my office please”

Dean immediately changed his course to the large oak doors, perfecting his professional smile and walking through. “You needed me, sir?”

Mr. Novak glanced up from his papers, a contemplative look upon his face. “Close the door” He demanded, his deep baritone voice dripping with authority and, Dean would dreamily describe, sex.

Dean obediently closed the office doors and promptly turned back to look at his boss who had now risen from his seat and was crossing the room towards him. 

“I have a …. Special request to ask of you, Dean” Mr. Novak’s deep timber voice echoed through the room.

“Of course sir, anything.” Dean replied perkily, knowing there wasn’t a thing out there he wouldn’t not do if it meant disappointing his boss so soon into his employment.

“I have um … let's just call it a need, a special need that I would like you fulfill.” Mr. Novak said delicately, as if Dean was a wild animal he didn’t want to scare off.

Dean smiled, “I am always happy to be of service to you, Mr. Novak, no matter what challenge.”

Mr. Novak smiled gratefully and gestured to follow him to another door on the other side of the room. “Follow me then,” Mr. Novak pushed open the door, “Oh, and please, call me Sir or Master when we’re in this room”

Dean stared at Mr. Novak confusedly but then stepped through into the room and understood immediately. The room big, filled with various sex toys, machines, and a large king sized bed at the center. Dean was no blushing virgin but even he had never been tried the intense, pain scene part of sex. That required a lot of trust from your partner that Dean never had.

Dean turned to look at his employer, thinking of his options. He could say no, walk out of here and act like nothing happened. If Mr. Novak fired him Dean would for sure win a wrongful termination lawsuit. Or, he could say yes. Afterall, Mr. Novak is a handsome man that if he had met in a bar he would’ve loved to have a one night stand with. Looks and attraction weren’t the problem but the trust was. He hadn’t known the man for long, hell, it hasn’t even been a full month of working for him. How desperate was Mr. Novak to come to his assistant to have sex with. But Mr. Novak was always calm and collected, professional and nice, he wouldn’t be such a bad choice if this was how Dean wanted to first experience the BDSM scene. 

Decision made, Dean hesitantly asked, “Should I … unclothe, Master?”

Mr. Novak, no, Master smiled brightly, “Yes, you may”

Dean slowly disrobed, looking around the room and trying to get accustomed to it. When he finally took the last layer off of his body he had to hold off the inane urge to cover himself up in front of Sir. He knew the basics of BDSM, he had to give himself entirely to his Dom and trust he would take care of him.

Master stared hungrily at him, as if he were a starving man seeing food for the first time. Dean wouldn’t lie and say he didn’t feel a bit proud of his physique he took such high care of.

“Before we can begin,” Master started, coming closer into Dean’s personal space, “I need to know your safe word.”

Dean blinked. Oh right. In case something went wrong. “Uh … Cranberry.”

Master’s mouth ticked up in amusement and nodded in agreement, “Alright, cranberry it is.”

Master walked over to a nearby dresser and pulled out a few things, from Dean could see it looked like a bottle of lube and a couple of toys to play with. He then came over to Dean, “Get on the bed”

Dean gulped, full of nerves of both excitement and fear at this new thing. He didn't know which way Master wanted him so he just laid on his back, legs spread apart for easy access. 

“No little one, on your stomach.”

Dean felt himself flush at the pet name but obediently turned to go on his stomach, ass now up in the air. The cool air in the room felt good against his warm flesh, goosebumps now covered the majority of his body. He then heard the sound of a cap being screwed off, hands rubbing together to warm it up, and soon enough a finger probed his hole.

“Now, just relax little one,” Master cooed while rubbing his lower back in an attempt to calm him down.

Dean took a deep breath in order to calm himself down and nodded, mentally preparing himself for what he signed up for. His breath hitched as the first finger pushed into him but soon enough his body stretched to accommodate the foreign invader. Master, after a few minutes, added another finger, further stretching him. It hurt at first, as prepping usually did, but Dean soon felt the tendrils of pleasure coming from the stimulation he was receiving. Dean let out a soft moan as Master continued his ministrations. He felt ready to be used now, to be fucked by this man. He decided to voice his opinions.

“More, I want more. Want you inside me”

Dean couldn’t see but he could hear Master’s harsh intake at the request. A few seconds went by and then … THWACK!

Dean froze stock still as what just happened hit him. It literally hit him. He had just been spanked by Master.

“Little ones dont demand, they obey.” Master said from behind him, “I’ll excuse you this time because this is new to us both but don’t make that mistake again. Understood?”

Dean could still feel the stinging in his ass from the smack, and oddly enough he liked it. It felt good, it felt real. “Yes Master.”

“Good.”

Master went back to fingering Dean, but this time added a third finger and started moving his fingers in and out at a faster pace than before. It was probably some kind of punishment for his behavior bot Dean couldn't care less. It felt amazing, to be stretched so wide and feel each individual digit inside his hole. What felt like 1 minute was probably more than 10, he felt the fingers leave his ass with a pop. He whimpered at the loss, desperately wanting the feeling of fullness back.

“Hush, I’m going to give you what you need now.”

Master shoved his giant meat sausage is Dean’s split peached asshole. Dean moaned like a fucking bitch in heat, his hole stretching to the limit in order to take on Master’s giant dong. Dean wished he would’ve privately prepped himself before, preferably in the window so God could see.

Master was hump fucking him fast and dirty, more dirty than that time Dean was in the bathroom after a spicy taco from taco bell, and by spicy he meant they accientally spilled a drop of hot sauce in his food. Things sped up, faster and faster. Dean could feel he was about to cum and shoved his hand underneath to him, trying to touch himself and bring himself to completion faster,

Within seconds Dean cried out, cum spurting out from his dick and all over the bed sheets below. Master was still pummeling him from behind, but he could tell his end was near as well by how fast he was going. And he was right. 30 seconds laters Master let out a long, deep moan and spilled his seed into Dean’s pert little ass.

Dean grinned as he felt Master collapse next to him, “So, Master, when’s round 2?”

Master let out a loud chuckle and snuggled up closer to Dean’s body, becoming the bigger spoon on the bed, “Just give me a few more minutes … and then you can meet Big Bertha”

**Author's Note:**

> Yes. Big Bertha is exactly what you think it is. Also yeah, you can tell its been rushed.


End file.
